Upgrading to Zope 2.8.x
From the RTFM-Department
When I started playing around with Plone 2.1 a couple of weeks ago I also tried using Zope 2.8.1 but encountered too many errors with my migrated Plone 2.0.x instances which disappeared when I did the same using ye' good ol' 2.7.7 - from which I (falsely) concluded, that Plone 2.1 just didn't really work with 2.8.1 regardless of what the requirements say.
In fact, all you need to do is to first update your catalogs i.e.
- install Zope 2.8.1 and Plone 2.1
- copy the Data.fs from your 2.7.x instance
- update the catalog
- migrate your Plone instance
Regarding step 3 it's advisable to RTFM (more precisely, the doc/FAQ.txt inside the Zope 2.8.1 directory):
To perform the migration:
- go to the ZMI
- click on your ZCatalog instance (or portal_catalog inside
your CMF or Plone instance)
- you will get an "AttributeError, _length"...don't panic
- call the "manage_convertIndexes" method of the ZCatalog
(by replacing the "manage_main" part of the URL with
"manage_convertIndexes")
- depending on the size of your ZCatalog the migration may
take a while
- after the conversion a message will appear: "Indexes
converted and reindexed"
While I'm not going to rush updating my existing 2.1/2.7.7 production sites (there's nothing really wrong per se with 2.7.7!) I am confident enough to use 2.8.1 for all new instances from now on - and now you can be too ;-)

Thanks
Thank you for your interestingly smooth geek-talk on Zope/Plone/Mac. It's way out of my expertise--I'm a middle school sci teacher--and I'm trying to get a new 2.1 plone/Zope 2.8.1/MacPython 2.4.1 to happen on my OS X 10.3.9 machine. I'm going to use this with my classes. Sometimes help docs are not that helpful and comments from blogs are better. Anything else you post on the topic I will appreciate. -David